CN110105187A - A kind of production method of 4- hydroxy-2-butanone - Google Patents
A kind of production method of 4- hydroxy-2-butanone Download PDFInfo
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- CN110105187A CN110105187A CN201910356631.XA CN201910356631A CN110105187A CN 110105187 A CN110105187 A CN 110105187A CN 201910356631 A CN201910356631 A CN 201910356631A CN 110105187 A CN110105187 A CN 110105187A
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- butanone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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Abstract
The invention discloses a kind of production methods of 4- hydroxy-2-butanone, belong to field of fine chemical, solve the problems, such as that existing synthetic method yield is lower.The present invention is warming up to 55-60 DEG C the following steps are included: 1,3-BDO, catalyst, auxiliary agent, water and water entrainer are added into reaction kettle；Hydrogen peroxide is added dropwise into mixed solution, vacuum distillation divides water；Stop that hydrogen peroxide is added dropwise, continues stirring 1-1.5 hours, water entrainer is steamed；Control system temperature is not higher than 60 DEG C, and rectification under vacuum obtains finished product 4- hydroxy-2-butanone.Auxiliary agent is added in the present invention, and 1,3-BDO is made preferably to participate in reacting, and improves conversion ratio；Chemical reaction of the invention carries out under condition of negative pressure, and control temperature is not higher than 60 DEG C, avoids the generation of butenone；In negative pressure system, reaction can be made sufficiently to carry out under cryogenic, product is easier to distill, and is not likely to produce impurity.
Description
Technical field
The invention belongs to field of fine chemical, and in particular to a kind of production method of 4- hydroxy-2-butanone.
Background technique
4- hydroxy-2-butanone, is commonly called as butanone alcohol, and the entitled 4-hydroxy-2-butanone of English is a kind of important
Medicine intermediate.It can be used for synthesizing six carbon alcohol, and six carbon alcohol are the important centres for synthesizing vitamin A (Retinol)
Body；A kind of warm fragrant perfume raspberry ketone with quiet and tastefully laid out fruity note can also be synthesized with phenol reactant；Addition is suitably urged
After agent, important industrial chemicals (R) -1,3-BDO can be synthesized, it can be used for synthesizing optical compound azacyclo-
Butanone is the intermediate feed of penem antibiotics, telergone, fragrance and insecticide synthesis；It can also be by 4- hydroxyl -2-
Butanone synthesizes (R) -3- amino butanol by biological enzyme, and (R) -3- amino butanol is the important source material for synthesizing Du Lutewei, degree
Lu Tewei is the anti-AIDS integrase inhibitor for being approved by the FDA in the United States listing for 2013.
The production method of butanone alcohol is generally condensed by formalin with acetone under alkaline condition.By formalin and
The mixed liquor and acetone of lye enter pipeline reactor by a certain percentage, and 51 ~ 53 DEG C of reaction temperature, control flow keeps reaction
Liquid stops 3 ~ 4min in reactor, and inflow fills in citric acid (stopped reaction)-acetone reactor tank, and flow back 10min,
Acetone is recycled, after boiling off moisture content, obtains the butanone alcohol crude product that content is about 80%.Have in entire reaction process a large amount of
Yuban, and impurity level is big, is easy to produce by-product butenone.
" a kind of synthetic method of 4- hydroxy-2-butanone " makees catalyst using sodium tungstate, and n-hexane is water entrainer, and product is received
Rate 65% or so, yield is lower, and industrialization production needs to be investigated.
Summary of the invention
The object of the present invention is to provide a kind of production methods of 4- hydroxy-2-butanone, to solve existing synthetic method yield
Lower problem.
The technical scheme is that a kind of production method of 4- hydroxy-2-butanone, comprising the following steps:
Step 1: addition 1,3-BDO, catalyst, auxiliary agent, water and water entrainer into reaction kettle, the auxiliary agent and catalyst
The amount of substance is identical, then stirs evenly, and forms mixed liquor, is warming up to 55-60 DEG C；
Step 2: while agitating, hydrogen peroxide is added dropwise into mixed solution, while vacuum distillation divides water, dioxygen is added dropwise in control
Water speed is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1-1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, above-mentioned reaction system rectification under vacuum is obtained into finished product 4- hydroxyl -2- fourth
Ketone, product vapor detection purity reach 95% or more.
As a further improvement of the present invention, in step 1,1,3-BDO, catalyst, water and water entrainer mole
Than for 1:0.02-0.024:5:0.4-0.5.
As a further improvement of the present invention, in step 1, auxiliary agent is tetrabutylammonium chloride.Cheap, effect is good.
As a further improvement of the present invention, in step 2, pressure is 0.01MPa in the system of vacuum distillation.
As a further improvement of the present invention, in step 2, the molar ratio of the 1,3-BDO and hydrogen peroxide is 1:
1-1.2。
As a further improvement of the present invention, water entrainer is diisopropyl ether.
As a further improvement of the present invention, catalyst is sodium molybdate.
As a further improvement of the present invention, in step 2, the mass fraction of hydrogen peroxide is 30%.
Preferably, in step 1,60 DEG C are warming up to；In step 3, continuing mixing time is 1.5 hours.
The reaction mechanism is as follows:
By mechanism it can be found that after reaching reaction end, if continuing heating stirring, finished product 4- hydroxy-2-butanone may
It is converted to butenone, so reaction temperature should be controlled.
Compared with the existing technology, the present invention achieve it is following the utility model has the advantages that
1, due to the poorly water-soluble of 1,3-BDO, it cannot participate in reacting during the reaction well, cause conversion ratio not high；
So auxiliary agent tetrabutylammonium chloride is added in the present invention, tetrabutylammonium chloride can make 1,3-BDO preferably participate in reacting, make
Reaction can be carried out preferably, improve conversion ratio；
If 2, reaction temperature is higher than 60 DEG C, as time increases, as described in above-mentioned mechanism, 4- hydroxy-2-butanone is easy to turn
It is melted into butenone；Chemical reaction of the invention carries out under condition of negative pressure, and control temperature is not higher than 60 DEG C, avoids the life of butenone
At；In negative pressure system, reaction can be made sufficiently to carry out under cryogenic, product is easier to distill, and is not likely to produce impurity；
3, it is water entrainer that the present invention, which selects diisopropyl ether, and price is lower than n-hexane or hexamethylene, and is had very strong anti-automatic
Oxidisability, peroxide not easily generated, prevents the generation of by-product in reaction process；
4, for the present invention using sodium molybdate as catalyst, cost is lower than sodium tungstate；
5, the method for the present invention easy post-processing, unconverted raw material can efficiently separate recovery, reduce production cost, subtract
Three waste discharge is lacked.
Specific embodiment
The following examples can further illustrate the present invention, but the invention is not limited in any way.
Embodiment 1,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 10000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 428kg, product gas
Mutually detection purity reaches 95% or more, and yield 73% recycles 1,3-BDO 110kg.
Embodiment 2,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 240mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 240mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 10000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.2 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 416kg, product gas
Mutually detection purity reaches 95% or more.Yield 71%.Recycle 1,3 butylene glycol 105kg.
Embodiment 3,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 5000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 10000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 410kg, product gas
Mutually detection purity reaches 95% or more.Yield 70%.Recycle 1,3 butylene glycol 108kg.
Embodiment 4,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 12000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.4 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 440kg, product gas
Mutually detection purity reaches 95% or more.Yield 75%.Recycle 1,3 butylene glycol 101kg.
Embodiment 5,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 240mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 240mol, water 50000mol and water entrainer diisopropyl ether 5000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 12000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1 hour, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 404kg, product gas
Mutually detection purity reaches 95% or more.Yield 69%.Recycle 1,3 butylene glycol 104kg.
Embodiment 6,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 220mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 220mol, water 50000mol and water entrainer diisopropyl ether 4500mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 11000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 410kg, product gas
Mutually detection purity reaches 95% or more.Yield 70%.Recycle 1,3 butylene glycol 109kg.
Embodiment 7,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 55
℃；
Step 2: while agitating, the hydrogen peroxide 12000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 404kg, product gas
Mutually detection purity reaches 95% or more, and yield 69% recycles 1,3-BDO 107kg.
Embodiment 8,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 5000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 58
℃；
Step 2: while agitating, the hydrogen peroxide 10000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.5 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 410kg, product gas
Mutually detection purity reaches 95% or more, and yield 70% recycles 1,3-BDO 106kg.
Embodiment 9,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 12000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1 hour, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 410kg, product gas
Mutually detection purity reaches 95% or more, and yield 70% recycles 1,3-BDO 107kg.
Embodiment 10,
Step 1: 1,3 butylene glycol 10000mol, catalyst sodium molybdate 200mol, four fourth of auxiliary agent are added into 3000 liters of reaction kettles
Ammonium chloride 200mol, water 50000mol and water entrainer diisopropyl ether 4000mol, stir evenly, and form mixed liquor, are warming up to 60
℃；
Step 2: while agitating, the hydrogen peroxide 10000mol that mass fraction is 30% being added dropwise into mixed solution, subtracts simultaneously
Esterification is pressed, pressure is 0.01MPa in system, and control is added dropwise dioxygen water speed and is consistent with vacuum distillation dehydration speed；
Step 3: stopping drop when the content of 1,3-BDO in gas chromatographic detection reaction kettle is not higher than the 25% of initial content
Add hydrogen peroxide, continue stirring 1.2 hours, the temperature controlled in reaction kettle is not higher than 60 DEG C, and water entrainer is steamed；
Step 4: control system temperature is not higher than 60 DEG C, rectification under vacuum obtains finished product 4- hydroxy-2-butanone 405kg, product gas
Mutually detection purity reaches 95% or more, and yield 69% recycles 1,3-BDO 109kg.
As can be seen from the above embodiments, the present invention makees catalyst using cheap sodium molybdate, and diisopropyl ether is water entrainer,
By negative pressure system, control the impurity content in entire reaction process, to improve reaction yield, yield reach 69% with
On, industrialization production cost is reduced, is had very important significance to industrialization production.
Claims (9)
1. a kind of production method of 4- hydroxy-2-butanone, it is characterised in that the following steps are included:
Step 1: addition 1,3-BDO, catalyst, auxiliary agent, water and water entrainer into reaction kettle, the auxiliary agent and catalyst
The amount of substance is identical, then stirs evenly, and forms mixed liquor, is warming up to 55-60 DEG C；
Step 2: while agitating, hydrogen peroxide is added dropwise into mixed solution, while vacuum distillation divides water, dioxygen is added dropwise in control
Water speed is consistent with vacuum distillation dehydration speed；
Step 3: when the content of 1,3-BDO in reaction kettle is not higher than the 25% of initial content stop that hydrogen peroxide is added dropwise, after
Continuous stirring 1-1.5 hours, the temperature controlled in reaction kettle are not higher than 60 DEG C, water entrainer are steamed；
Step 4: control system temperature is not higher than 60 DEG C, above-mentioned reaction system rectification under vacuum is obtained into finished product 4- hydroxyl -2- fourth
Ketone.
2. a kind of production method of 4- hydroxy-2-butanone according to claim 1, it is characterised in that: in step 1, institute
The molar ratio for stating 1,3 butylene glycol, catalyst, water and water entrainer is 1:0.02-0.024:5:0.4-0.5.
3. a kind of production method of 4- hydroxy-2-butanone according to claim 2, it is characterised in that: in step 1, institute
Stating auxiliary agent is tetrabutylammonium chloride.
4. a kind of production method of 4- hydroxy-2-butanone according to any one of claim 1-3, it is characterised in that:
In step 2, pressure is 0.01MPa in the system of vacuum distillation.
5. a kind of production method of 4- hydroxy-2-butanone according to claim 4, it is characterised in that: in step 2, institute
The molar ratio for stating 1,3 butylene glycol and hydrogen peroxide is 1:1-1.2.
6. a kind of production method of 4- hydroxy-2-butanone according to claim 5, it is characterised in that: the water entrainer is
Diisopropyl ether.
7. a kind of production method of 4- hydroxy-2-butanone according to claim 6, it is characterised in that: the catalyst is
Sodium molybdate.
8. a kind of production method of 4- hydroxy-2-butanone according to claim 7, it is characterised in that: in step 2, institute
The mass fraction for stating hydrogen peroxide is 30%.
9. a kind of production method of 4- hydroxy-2-butanone according to claim 8, it is characterised in that: in step 1, rise
Temperature is to 60 DEG C；In step 3, continuing mixing time is 1.5 hours.
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| CN114853588A (en) * | 2022-06-09 | 2022-08-05 | 福州大学 | Separation process of reaction liquid for supercritical synthesis of butanone alcohol |
| CN115124412A (en) * | 2022-07-01 | 2022-09-30 | 清源创新实验室 | Energy-saving separation process for synthesizing butanone alcohol reaction liquid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114853588A (en) * | 2022-06-09 | 2022-08-05 | 福州大学 | Separation process of reaction liquid for supercritical synthesis of butanone alcohol |
| CN115124412A (en) * | 2022-07-01 | 2022-09-30 | 清源创新实验室 | Energy-saving separation process for synthesizing butanone alcohol reaction liquid |
| CN115124412B (en) * | 2022-07-01 | 2023-11-21 | 清源创新实验室 | Energy-saving separation process for synthesizing butanone alcohol reaction liquid |
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